Can you identify this Maico?

It looks like an 82 or 83 GS given the single shock.  I can't make out the displacement, but I would guess one of the open class variations.

Wondering if the H&H on that jersey has anything to do with the H&H Music Co. Racing Team?

H&H was Barry Higgins dealership in GA

It's an 83 GS model

I can't answer if it was affiliated with H&H Music, but H&H was a KTM dealership in Georgia owned by AMA Hall of Famer Barry Higgins (who likely sold other European brands as well like Maico). I bought a new '92 KTM 250SX from him and had it shipped to Michigan. Only bike I ever bought in a crate (and one of the rare KTMs on the Michigan motocross tracks back in the day). 

http://hof.motorcyclemuseum.org/detail.aspx?RacerID=194

1982 490 Alpha E would be my guess, says it right there on the seat

I knew that, but was drawing a blank! Dang it!

Looks like an '82 Alpha E and as I recall they only did a 250 and a 490 in that model.  No 440's after '81.

All this time I thought it was just called A Bad Ass Maico Enduro!

I’d say 82 from the looks of clutch cover and case shape but I could be wrong. 
Everyone with H&H being Barry Higgins is correct. 

Works for me...  

Ape is correct, 82 490 GS

Your dad was a badass for sure racing a 490, but how about racing in the south in those thick padded leathers?

I think that picture is from a test in Dirt Bike.  The ads for the Maicos were amazing in that period.  I’ll see if I can find one.

Kick stand days but looks like a large piece of metal holding it up 

 My '79 GS AW400. I had the headlight off to race a rocky hare scramble next weekend. Loved it,still hunting for it. The bike,not the headlight  lol. Notice the Fox air shox.

Definitely an 82 model. Definitely. Yeah, like for sure.

That is the one!  Thanks for posting it.  How could you not want to buy one??

I really liked those early 80’s off-road bikes.

Woods Tank! A real manly man's bike.